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Diastereoselective Synthesis of Cephalotaxus Esters via Asymmetric Mukaiyama Aldol Reaction

Author:
Ma, Guo-Zhen, Li, Peng-Fei, Liu, Lu, Li, Wei-Dong Z., Chen, Li
Source:
Organic letters 2017 v.19 no.9 pp. 2250-2253
ISSN:
1523-7052
Subject:
Cephalotaxus, carbon, chemical reactions, chemical structure, diastereoselective synthesis, diastereoselectivity, esters
Abstract:
We report a protocol for efficient stereoselective installation of the chiral oxygen-containing tetrasubstituted tertiary carbon stereocenter of the side chain of cephalotaxus esters by means of highly diastereoselective Mukaiyama aldol reactions between α-keto esters (2) and a (Z)-α-chloro ketene silyl acetal. This protocol permitted synthesis of cephalotaxus esters including six natural products in good to excellent yields (up to 94%) with high diastereoselectivities (dr up to 97:3) and could be performed on a multigram scale.
Agid:
5794029